Liman became attached to direct "Swingers" when its screenwriter Jon Favreau turned down offers from studios who wanted to cast established actors. The director agreed to cast Favreau and his friends (Vince Vaughn, Ron Livingston and Patrick Van Horne) in this comedy about struggling actors amid the L.A. club milieu. Centered around a group of friends trying to snap a heartbroken buddy (Favreau) out of his lovesick funk, the film featured a good bit of swaggering hipness and self-conscious posturing but was strongly grounded in genuine sweetness. Made on a budget of $250,000, the dialogue-propelled "Swingers" was often filmed on locations without permits in a pseudo-documentary style. The result was a film filled with energy and charm that captivated audiences and critics and not only established a cult following, but also jump-started the careers of the featured actors, most notably Vaughn.

Artful, smart and exhilarating, Liman's rapid-paced next effort "Go" (1999) more than lived up to the legacy of the acclaimed "Swingers". A refreshingly optimistic and affirming take on John August's script about young Los Angelenos on the fast track, "Go" was comprised of three separate but related sections, each focusing on different members of the film's talented ensemble of up and comers. Liman showed a rare filmmaker's economy, bringing in this elaborate and energetic ride at well under two hours. Doing double duty as cinematographer, Liman created a look for the film that stylistically captured both the script's vivid spirit and somewhat dark subject matter. The director shot some especially visually arresting scenes, including an Ecstasy-fueled hallucination set in a supermarket, a terrifying neon lit Las Vegas strip car chase and a hazy rave dance floor scene. The film received overwhelmingly positive reviews but box office returns were comparably lackluster. Marketed as a teen movie because of its hip, young cast, the exceptional film was lost in the influx of insipid commercial teen fare. Following "Go", Liman produced the Sarah Thorp film "See Jane Run" (2001), starring Clea DuVall and Kevin Corrigan, and as producer he helped bring the indie lesbian comedy "Kissing Jessica Stein" (2001) to the screen.

Liman enjoyed his most potent commercial and creative success when he helmed the top-notch, cleverly assembled action thriller "The Bourne Identity" (2002), an adaptation of author Robert Ludlum's potboiler that cast Matt Damon as Jason Bourne, an amensiac who washes ashore and finds himself uncannily equipped to battle the assassins pursuing him as he tries to piecce together his identity. Building on his success, he served as an executive producer and directed the pilot episode of the smash hit Fox melodrama "The O.C." (2003 - ), which followed the turbulent relationships of a group of Orange County teens and their parents and made stars out of newcomers Mischa Barton, Benjamin McKenzie, Adam Brody and Rachel Bilson. Liman's momentum continued when he directed "Mr. & Mrs. Smith" (2005), a crackerjack comedic thriller about an increasingly distant married couple who discover they're each secretly high-caliber assassins when they're assigned to kill one another, which reignites their ardor. In addition to Liman's characteristically innovative action staging, the film benefitted greatly from the chemistry between stars Brad Pitt and Angelina Jolie, who developed a controversial, high-profile relationship off-screen while making the film. In 2005 he signed on the direct the pilot episode of "Heist," about a season-long attempt to rob three jewelry stores on Beverly Hills' swanky Rodeo Drive, for NBC.